So many models, so little Leo DiCaprio

Meet the enemy of monogamy

He doesn’t have an Oscar, allegedly turned down a role in Star Wars and the last time we checked, he was still single. But don’t feel too bad for Leo DiCaprio. He’s got 20 tanned and toned shoulders to cry on. After ending his on-off relationship with Victoria’s Secret model Toni Garrn earlier this year, the 40- year old Hollywood star reportedly emptied the VIP section of a Miami nightclub, taking 20 female guests home with him. This, of course, is just another day in the life of the serial bachelor aka future Hugh Hefner. Check out his incredible relationship timeline since the turn of the century.

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Gisele Bündchen

2000-2005

Gisele Bündchen probably kicked off Leo’s leggy blonde addiction. She reportedly broke off their five-year relationship due to his party boy ways.

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Sienna Miller

2005

British actress Sienna Miller apparently had a short-lived fling with Leo to get back at then-boyfriend Jude Law. We’re sure Leo didn’t mind.

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Bar Refaeli

2006-2009

He may have ADD when it comes to relationships ( we use this word loosely), but Israeli model Bar Refaeli managed to hold his attention until 2009 and then piqued his interesst again from 2010 to 2011. Too bad there are so many models and not enough Leo to go around.

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Ashley Roberts

2009

Striking “Get with a Pussy Cat Doll” off his to-do list in 2009, Leo was briefly spotted with Ashley Roberts.

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Emma Miller

2009

With no movies out that year, Leo clearly had an abundance of time on his hands and some gorgeous women willing to spend it with him. Emma Miller is believed to have dated him during his break from Refaeli in July 2009.

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Anne Vyalitsyna

2009

If all his alleged women of 2009 got together, we would only be a few models short of a calendar shoot. But the Kingfisher calendar hasn’t seen the likes of this Russian Victoria’s Secret bombshell, Anne Vyalitsyna.

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Blake Lively

2011

No, you are not currently looking at your list of fantasy women. At this point, we suggest you just try and live vicariously through Leo. You probably never had a chance with Blake Lively anyway.

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Ashley Crawford

2011

He may have been Down Under filming The Great Gatsby, but Leo was busy playing Titanic with Australian model Alyce Crawford.

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Madalina Ghenea

2011

Everyone knows the harder it is to pronounce a model’s name, the hotter she is. We bet Leo just called Romanian-born Italian model Madalina Ghenea “babe”.

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Erin Heatherton

2011-2012

With Erin Heatherton on the list, we can safely assume that the Victoria’s Secret Fashion show is just an elaborate audition for “Who Wants To Date DiCaprio?”

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Toni Garrn

2013-2014

Victoria’s Secret Angel Garrn was the Rolls-Royce of leggy blondes. We guess Leo will just have to settle for 20 Audis…

Chelsey Weimar

Most people browse the Victoria’s Secret catalogue for lingerie. Leo likes to browse for his next girlfriend. The latest VS fledgling Leo has added to cart the list is 19-year-old Chelsey Weimar, who fronts the Victoria’s Secret Pink campaign. Barely legal and barely clothed, Leo proves he knows how to celebrate an Oscar win… or you know, a casual Tuesday.